Diisobutylaluminum Hydride
Diisobutylaluminum Hydride - Related Videos
01:17
Esters to Alcohols: Hydride Reductions
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2025
Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of the reducing agent and proceeds via an aldehyde intermediate. Lithium aluminum hydride is a source of hydride ions and functions as a nucleophile. The mechanism proceeds in three steps. Firstly, the nucleophilic hydride ion attacks the carbonyl carbon of the ester to form a tetrahedral intermediate. Subsequently, the carbonyl group re-forms,...
01:17
Carboxylic Acids to Primary Alcohols: Hydride Reduction
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2025
Carboxylic acids, upon reaction with strong reducing agents such as lithium aluminum hydride followed by hydrolysis, undergo reduction to form primary alcohols. Weaker reducing agents like lithium tri-tert-butoxyaluminum hydride or diisobutylaluminum hydride cannot reduce carboxylic acids to primary alcohols. Carboxylic acids can also be reduced to primary alcohols by using borane in the tetrahydrofuran solvent. The main advantage of using borane in reducing a carboxylic acid is that this...
08:21
Determination of Inorganic Arsenic in a Wide Range of Food Matrices using Hydride Generation - Atomic Absorption Spectrometry.
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Cited by 12 •
2017
The usefulness of an analytical method to determine inorganic arsenic in a wide range of food matrices is demonstrated. The method consists of selective extraction of inorganic arsenic into chloroform with a final determination by hydride generation-atomic absorption spectrometry.
01:26
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
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2023
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct. The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
09:05
Supercritical Nitrogen Processing for the Purification of Reactive Porous Materials
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Cited by 9 •
2015
Nitrogen is an effective supercritical fluid for extraction or drying processes due to its small molecular size, high density in the near-liquid supercritical regime, and chemical inertness. We present a supercritical nitrogen drying protocol for the purification treatment of reactive, porous materials.
FAQs
The bulky aluminum center transfers hydride to an organic substrate while limiting how readily the reaction can continue. This steric environment helps distinguish partial reduction from deeper reduction, allowing chemists to control the oxidation state reached by carbon-containing compounds. The result is especially useful when an aldehyde is needed as an intermediate rather than the more reduced alcohol.
Low temperature and a limited amount of DIBAL-H help restrain the extent of reduction. If conditions permit the reaction to proceed further, a substrate intended to stop at the aldehyde stage may instead undergo additional reduction to an alcohol. Controlling these variables therefore determines whether the reaction provides a partially reduced product or a more extensively reduced one.
Esters and nitriles are important substrate classes for DIBAL-H chemistry because their reduction can be directed toward useful aldehyde-stage products under carefully controlled conditions. This behavior gives chemists a way to alter the oxidation state of carbon-containing molecules without necessarily reducing them as far as alcohols, supporting the preparation of intermediates for later synthetic steps.
DIBAL-H provides a means of studying and manipulating how carbonyl-containing compounds respond to hydride transfer. Rather than treating reduction as an all-or-nothing process, chemists can use temperature and reagent quantity to favor a selected oxidation state. This controlled reactivity is valuable when an aldehyde must remain available for subsequent transformations in a multistep sequence.
The reaction requires dry conditions because DIBAL-H reacts readily with moisture. Chemists must therefore exclude water during the reaction and prepare an appropriate aqueous workup for the end of the procedure. These two stages serve different purposes: dryness preserves the reagent during reduction, while the aqueous treatment processes the reaction mixture after the desired transformation has been completed.
DIBAL-H is useful when a synthesis needs an aldehyde intermediate at a defined point in the sequence. Converting a suitable ester or nitrile to that oxidation state creates a functional group that can support subsequent synthetic operations. Its value lies in combining substrate scope with control over reduction depth, rather than simply maximizing conversion to the most reduced product.